Acetic Acid → 2-Hydroxymethyl-1-methylimidazo[4,5-c]pyridine

HRID 1601844Notes

Reaction equation

HRID 1601844 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]([CH3:19])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1)(C(C)(C)C)(C)C.O1CCCC1.C(O)(=O)C>O>[OH:8][CH2:9][C:10]1[N:11]([CH3:19])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 232983402-t-Butyldimethylsilyloxymethyl-1-methylimidazo[4,5-c]pyridine

Product 1

HCID 232983682-Hydroxymethyl-1-methylimidazo[4,5-c]pyridineYield 111.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.00 g of 2-t-butyldimethylsilyloxymethyl-1-methyl-1H-imidazo[4,5-c]pyridine (prepared as described in Preparation 72) in 60 ml of a 1:1:1 by volume mixture of tetrahydrofuran, acetic acid and water was stirred at room temperature for 1 hour and then at 60° C. for 5 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation. The resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate and then concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 1.97 g of the title compound, melting at 285-290° C.

Workup

  1. waitat 60° C. for 5 hours
  2. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation
  3. additionThe resulting residue was mixed with an aqueous solution of sodium hydrogencarbonate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe concentrate was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-f84ebd1157f84eaab917ba7b27795812
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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